Polycyclic aromatic hydrocarbon compounds containing an S atom or S(=O)2 group in their basic structure

Patent metadata

Field	Value
Publication number	US-9505869-B2
Application number	US-201514719842-A
Country	US
Kind code	B2
Filing date	May 22, 2015
Priority date	Nov 23, 2011
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

Polycyclic aromatic hydrocarbon compounds having an S atom or S(═O) 2 moiety incorporated in their basic polycyclic structure that can have a nitrogen-containing heterocycloaliphatic group and/or a substituted or unsubstituted phenoxy group and/or a polymeric moiety bonded to the polycyclic structure and to compositions such as, e.g., printing inks which comprise these polycyclic aromatic hydrocarbons as colorants.

First claim

What is claimed is:

1. A polymer, wherein at least about 0.1% of polymer molecules have bonded thereto 1 to 4 residues of formula -Q-(Y) w wherein Q represents a moiety of formula (A), (A′), (B), or (B′);

wherein Z represents O, S or N—R;
wherein X, which can be the same or different, represents O, S, or NR′; and
R and R′ independently represent an optionally substituted aliphatic, cycloaliphatic, aromatic, hetero aromatic, alkylaryl, alkylheteroaryl, arylalkyl or heteroarylalkyl group having from 1 to about 20 carbon atoms; and R and R′ may also be combined to form, together with the N atoms to which they are attached, an optionally substituted and/or fused 5- to 7-membered ring;
Y is selected from (i) halogen and (ii) optionally substituted N-heterocycloaliphatic groups having from 3 to about 8 ring members, at least one of which is N, which are bonded to Q through an N atom, and/or an optionally substituted phenol group which is bonded to Q through the O atom provided that at least one Y represents (ii);
w represents an integer of from 1 to 4; and
further provided that Q may at the same time be bonded to up to 4 polymer molecules.

2. The polymer of claim 1 , wherein the polymer is [[a compound]] of general formula (2):

wherein the groups R 4 , the same or different from each other, are selected from C 1 -C 10 alkyl and C 1 -C 4 alkoxy;
m represents an integer of from 1 to about 30;
n represents an integer of from 1 to about 3.

3. Optionally substituted compound of formula (B) or (B′):

wherein Z represents O, S or N—R, and X, which can be the same or different, represents O, S, or NR′; and
R and R′ independently represent an optionally substituted aliphatic, cycloaliphatic, aromatic, hetero aromatic, alkylaryl, alkylheteroaryl, arylalkyl or heteroarylalkyl group having from 1 to about 20 carbon atoms; and R and R′ may also be combined to form, together with the N atoms to which they are attached, an optionally substituted and/or fused 5- to 7-membered ring.

4. The compound of claim 3 which is unsubstituted.

5. The compound of claim 3 , wherein the compound is a compound of one of formulae (C) or (D) or (E) or (F) or (G) or (H):

wherein in the case of formula (E) and (H), Z represents O, S or N—R; and X, which can be the same or different, represents O, S, or NR′; and
R and R′ independently represent an optionally substituted aliphatic, cycloaliphatic, aromatic, hetero aromatic, alkylaryl, alkylheteroaryl, arylalkyl or heteroarylalkyl group having from 1 to about 20 carbon atoms; and R and R′ may be combined to form, together with the N atoms to which they are attached, an optionally substituted and/or fused 5- to 7-membered ring;
R 1 , R 2 and R 3 are independently selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl-COOH, C 1 -C 4 alkyl-SO 3 H, C 1 -C 4 alkoxy, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, C 1 -C 4 aminoalkyl, halogen, cyano, nitro, and SO 3 H, the alkyl groups being optionally substituted;
Y is selected from (i) halogen and (ii) optionally substituted N-heterocycloaliphatic groups having from 3 to about 8 ring members and which are bonded to an aromatic ring through an N atom; and (iii) optionally substituted phenoxy groups which are bonded to an aromatic ring through an O atom, the phenoxy group may be substituted by one or more substituents selected from halogen, nitro, cyano, NRR′, SO 3 H and COOH and salts and derivatives of these sulfonic and carboxylic acid groups, OH, heterocycloalkyl comprising up to three heteroatoms selected from O, N and S as ring members and from 3 to about 8 ring members, and alkyl (including cycloalkyl) and alkoxy (including cycloalkoxy) groups comprising from 1 to about 10 carbon atoms;
P represents a polymeric moiety having at least three repeating units which comprise an optionally substituted phenyl ring; and
x is an integer of from 0 to 4; and w is an integer of from 0 to 4.

Assignees

• Sicpa Holding Sa

Inventors

• Pasquier Cecile
• Wyss Patrick

Classifications

• C07D495/16 Primary

  Peri-condensed systems · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B57/08

  Naphthalimide dyes; Phthalimide dyes · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• C08G8/28 Primary

  Chemically modified polycondensates · CPC title